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Name	ISOEUGENOL	EINECS	202-590-7
CAS No.	97-54-1	Density	1.074 g/cm³
PSA	29.46000	LogP	2.43390
Solubility	N/A	Melting Point	-10 °C
Formula	C₁₀H₁₂O₂	Boiling Point	266.64 °C at 760 mmHg
Molecular Weight	164.204	Flash Point	122.907 °C
Transport Information	N/A	Appearance	light yellow-green viscous liquid
Safety	26-36-36/37	Risk Codes	22-36/37/38-43
Molecular Structure		Hazard Symbols	Xn
Synonyms	Phenol,2-methoxy-4-(1-propenyl)- (9CI);Phenol, 2-methoxy-4-propenyl- (8CI);1-(3-Methoxy-4-hydroxyphenyl)-1-propene;2-Methoxy-4-(1-propenyl)phenol;2-Methoxy-4-propenylphenol;3-Methoxy-4-hydroxy-1-propenylbenzene;4-Hydroxy-3-methoxy-1-propenylbenzene;4-Hydroxy-3-methoxy-b-methylstyrene;4-Propenylguaiacol;NSC 6769;iso-Eugenol;	Article Data	66

ISOEUGENOL Synthetic route

: 97-53-0
4-allylguaiacol

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With rhodium(III) chloride; ethanol at 140 - 145℃;	99%
With tris(triphenylphosphine)ruthenium(II) chloride at 50 - 60℃; for 4h; Temperature;	99%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; polydimethylsiloxane In methanol; water at 100℃; for 20h;	82%

: 1-(4-hydroxy-3-methoxyphenyl)prop-1-yl acetate

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 2h;	94%

: 1350619-56-5
2-methoxy-4-(1-propenyl)phenyl tetrahydro-2H-pyran-2-yl ether

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With iron(III) p-toluenesulfonate hexahydrate In methanol at 20℃; for 2h;	76%

: 97-53-0
4-allylguaiacol

: 124-38-9
carbon dioxide

A: 97-54-1
2-methoxy-4-propenylphenol

B: (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-enoic acid

Conditions

Conditions	Yield
With trimethylaluminum; cesium fluoride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; cobalt acetylacetonate In N,N-dimethyl acetamide; toluene at 60℃; under 760.051 Torr; for 12h; Inert atmosphere; Sealed tube; regioselective reaction;	A 25 %Spectr. B 72%

: 1530-32-1
ethyltriphenylphosphonium bromide

: 121-33-5
vanillin

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With potassium carbonate In water for 1.5h;	68%
With potassium carbonate In water at 25℃; for 1.5h; Product distribution; var. temp. and solvents;

: 97-53-0
4-allylguaiacol

: 201230-82-2
carbon monoxide

A: 97-54-1
2-methoxy-4-propenylphenol

B: 91142-61-9
5,6-Dihydro-3-methoxy-naphth-2-ol

C: 40275-47-6
3-(4-hydroxy-3-methoxyphenyl)-2-methylpropanal

Conditions

Conditions	Yield
With acetylacetonatodicarbonylrhodium(l); phosphoric acid; hydrogen; methoxybenzene; triphenylphosphine In dichloromethane at 110℃; under 15514.9 Torr; for 2h; Autoclave;	A 21 %Chromat. B 60% C n/a

: 4-(1-acetoxypropyl)-2-methoxyphenyl pivalate

A: 97-54-1
2-methoxy-4-propenylphenol

B: isoeugenyl pivaloate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 31h;	A 25.2% B 41.3%

: 4-(1-acetoxypropyl)-2-methoxyphenyl benzoate

A: 97-54-1
2-methoxy-4-propenylphenol

B: 2-methoxy-4-(prop-1-enyl)phenyl acetate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 12h;	A 36% B 9%

: 95316-34-0
3-Hydroxy-1-methoxy-2-(2-methoxy-phenoxy)-1-(4-hydroxy-3-methoxy-phenyl)-propan

A: 2785-87-7
2-methoxy-4-n-propylphenol

B: 97-54-1
2-methoxy-4-propenylphenol

C: 90-05-1
2-methoxy-phenol

Conditions

Conditions	Yield
With 10% nickel/activated carbon; hydrogen In 1,4-dioxane at 150℃; under 15001.5 Torr; for 2h; Autoclave;	A 5.5% B 14.2% C 19.3%

: 95316-34-0
3-Hydroxy-1-methoxy-2-(2-methoxy-phenoxy)-1-(4-hydroxy-3-methoxy-phenyl)-propan

A: 97-54-1
2-methoxy-4-propenylphenol

B: 90-05-1
2-methoxy-phenol

Conditions

Conditions	Yield
With 10% nickel/activated carbon; hydrogen In tetrahydrofuran at 150℃; under 15001.5 Torr; for 1h; Autoclave;	A 9.4% B 12.2%

ISOEUGENOL Chemical Properties

Synonyms: 4-PROPENYLGUAIACOL;4-PROPENYL-2-METHOXYPHENOL;4-HYDROXY-3-METHOXY-1-PROPENYLBENZENE;3-METHOXY-4-HYDROXYPROPENYLBENZENE;2-METHOXY-4-PROPENYLPHENOL;2-METHOXY-4-((E)-PROPENYL)-PHENOL;
ISOEUGENOL is the chemical compound with the formula C₁₀H₁₂O₂ .Its Molecular Weight is 164.2 .
Melting point:-10 °C
Boiling point:266 °C
density:1.082 g/mL at 25 °C
vapor density:>1 (vs air)
vapor pressure:<0.01 mm Hg ( 20 °C)
refractive index n20/D 1.575(lit.)
Flash point:>230 °F
storage temp.:0-6°C

ISOEUGENOL Uses

ISOEUGENOL's used as flavor intermediates.

ISOEUGENOL Toxicity Data With Reference

1.	skn-man 16 mg/48H MOD	CTOIDG Cosmetics and Toiletries. 94 (8)(1979),41.
2.	skn-rbt 100 mg/24H SEV	CTOIDG Cosmetics and Toiletries. 94 (8)(1979),41.
3.	skn-gpg 100 mg/24H SEV	CTOIDG Cosmetics and Toiletries. 94 (8)(1979),41.
4.	sce-hmn:lym 250 µmol/L	MUREAV Mutation Research. 169 (1986),129.
5.	orl-rat LD50:1560 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),378.
6.	orl-gpg LD50:1410 mg/kg	FCTXAV Food and Cosmetics Toxicology. 2 (1964),327.

ISOEUGENOL Consensus Reports

Reported in EPA TSCA Inventory.

ISOEUGENOL Safety Profile

Moderately toxic by ingestion. A moderate human skin irritant. Human mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and fumes. See also EUGENOL.

ISOEUGENOL's Hazard Codes:Xn
ISOEUGENOL's Risk Statements:
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
43:May cause sensitization by skin contact
ISOEUGENOL's Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany:2

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